Premier Experience + National Stature

Now for the details.  To his federal tax-dispute practice, Tom brings several key elements:

• 40 years of technical tax experience, first representing the IRS and, after that, representing blue-chip taxpayers
• 14 years of federal government service in Washington, D.C., where he represented the IRS in courts around the nation and in Washington.
• Over a decade of experience as a partner or shareholder with the nation’s largest and most prestigious international law firms;
• 42 years of extensive first-chair, in-court, trial and appellate experience, with the result that his name appears on over 60 reported federal court opinions — almost always in a first-chair role
• Five years as a prosecutor in his native Wisconsin, including both a stint as a federal prosecutor in Madison, and a stint as the youngest District (County) Attorney in Wisconsin

This “360-degree,” tax- and litigation-heavy combination enhances Tom’s ability to realistically assess the legal hazards faced by a taxpayer involved in an administrative dispute with the IRS; to plot, pursue, and implement a strategy for an administrative settlement with the IRS that comprehends the inner workings of both the IRS and the U.S. Department of Justice; and seamlessly to move ahead, if necessary, into IRS Appeals and then into litigation, through and including any courthouse appeals that are taken.

Tom is one of a handful of tax lawyers in private practice nationally to have first-chaired more than 20 jury trials and more than a dozen appeals in the federal courts. He has argued 15 cases before five federal courts of appeals — an extreme rarity for a tax lawyer in private practice.  With his award-winning, supervisory experience at the Department of Justice in DC and as a long-time partner with premier large law firms, Tom may have first-chaired more multi-million dollar tax-refund suits in the federal trial courts than any attorney now active in private practice in the United States. Tom estimates that overall he has litigated more than 200 federal tax cases over the last 40 years, on “both sides of the ball.”  In recent years, he is best known for his first-chair handling of cutting-edge federal tax-refund suits in which he “choreographed” multiple, similar pending seven- and eight-figure suits.  He recently first-chaired a proposed class action seeking $500 to $600 million in additional interest for the nation’s incorporated tax-exempt teaching hospitals — probably the largest federal tax class action in history, in terms of dollars and blue-chip members.  Tom is the only attorney in private practice in the nation, of whom he is aware, who formerly worked in both a district-court section (five years) and in the Court of Federal Claims section (nine years) of the Tax Division of the U.S. Department of Justice, in DC.

Tom’s highly unusual extensive-tax-plus-extensive-litigation skill set allows a taxpayer to avoid the “two headed” arrangement for handling contentious tax cases, where a law-firm Tax partner is “yoked” to a Litigation partner — a less-than-optimal, expensive arrangement used by most law firms.  Ask:  who will eventually argue the case in the trial court or the appellate court — the Litigation partner (trained in argumentation and the presentation of evidence), or the Tax partner (possessing the technical tax knowledge)?  Another drawback is that a “team” of lawyers naturally involves expensive “let’s educate ourselves” back-and-forth between and among disparate members of the team.

In addition to his in-court practice, Tom has advised or represented many taxpayers before the IRS’s Examination, Collection, Appeals, and Criminal Investigation Divisions, and before the IRS National Office.  Tom is the revisor/co-author of BNA/Bloomberg’s chapter, in its Tax Practice Series treatise, addressing IRS examinations and appeals.  In the IRS administrative context, Tom’s tax-litigation experience is a rare asset that facilitates a proper assessment of risk, and a clear view of the road ahead if the matter cannot be promptly settled with the IRS.  The presence of a tax lawyer with Tom’s stature demonstrates a taxpayer’s readiness effectively to meet incorrect determinations.  

Tom has worked with, or opposite, the IRS since 1982, when, as a young federal prosecutor, he handled his first federal tax case — a criminal case tried against Wisconsin’s top tax lawyer that went to a jury verdict of guilty and then, successfully, to the U.S. Court of Appeals for the Seventh Circuit where (with Tom in the first chair) it established a rule on an issue of first impression in that circuit.

With the IRS now going forward with its promised High Net-Worth audits, Tom offers unusual assistance:  he has handled both IRS administrative and litigation in this arena, as well as matters involving delinquent filings of foreign financial account reports, FinCen 114 (formerly known as Forms TD F 90-22.1),  also known as FBARs.  Resident aliens can find themselves surprised by the requirement that they file an FBAR, and Tom has successfully resolved those filing delinquencies for many clients.

 With a background as a former federal prosecutor, as a USDOJ Tax Division supervisor, and with extensive familiarity with FinCEN’s foreign-bank-account reporting regime, Tom is superbly situated to assist taxpayers who have failed to report income associated with virtual currency/cryptocurrency, such as Bitcoin.  Tom is very familiar with IRS programs for advantageously handling delinquencies of varying degrees of seriousness. 

Tom has extensive experience with federal payroll/employment/self-employment tax issues, probably having handled more diverse and more large-dollar cases in this arena than any other attorney in private practice in the U.S.  A business’s failure to pay over withheld employment taxes is a serious matter because the IRS sometimes brings criminal cases against the persons responsible for the failure.   Among his IRS representations were his successful, first-chair handling of tax-refund suits brought by the NFL’s Buffalo Bills football team, by LTV Steel, and by Marquette University.

Tom spent a substantial part of his career “chasing bad guys.”  For example, he handled for the IRS efforts to obtain financial records respecting a taxpayer suspected of murdering his sister to obtain insurance proceeds.  After extensive litigation in five or six states, federal courts ordered production of the records; but on the day before the taxpayer’s attorney was to produce the records to the IRS criminal investigator, the taxpayer murdered his attorney.  In another case that Tom handled for the IRS, he won, after a five-day trial, an order concluding that a brother and sister, a lawyer and CPA respectively, had conspired to help delinquent taxpayers make fraudulent transfers of their farms to put property beyond the IRS’s reach.  Very few lawyers practicing in the tax realm have experience handling criminal cases in court; and no accountants have handled criminal cases in court.  Tom has five years of experience in that “crucible.”

Tom’s taxpayer-side work in cases with large criminal overtones has included some very high-profile representations.  He represented a lawyer who was perhaps the IRS Criminal Division’s top target during a ten-year period.  More recently, he represented the owner of a chain of tax-return-preparation businesses who was one of the IRS Criminal Division’s top targets, who was attempting to avoid having the IRS shut down his business and also avoid having those civil-side defense efforts used against him in a subsequent criminal prosecution.  His experience as a former federal prosecutor may have been reassuring to these clients.

At an extreme end of the technical-tax spectrum is Tom’s work with what are widely considered to be the most complex substantive provisions of the Internal Revenue Code — those found in subchapter L, respecting the income taxation of insurance companies.  When Tom arrived in the DOJ Tax Division’s Court of Federal Claims Section in 1989, he was immediately assigned to first-chair several pending cases arising under subchapter L, with an aggregate value at the time approaching $1 billion.  Nine years later, in 1998, Tom accepted a partnership position from a private law firm in DC, familiar with his work at DOJ, that focused its practice upon the taxation of insurance companies under subchapter L.  QED.

Beginning in 2004, Tom was at the forefront of the landmark litigation over FICA tax paid on stipends provided to medical residents – litigation that in March 2010 led the IRS to announce a billion-dollar-plus global concession of the issue. Tom first-chaired the landmark victories for The University of Chicago Hospitals in both the federal district court and then in the U.S. Court of Appeals for the Seventh Circuit.  This reversal, by the IRS, of its long-time litigation position respecting an issue worth billions of dollars is one of the most notable IRS capitulations in history.  At the time of this capitulation, Tom was lead counsel in more of the pending FICA-tax cases than any other attorney in the nation.  He is the only attorney identified by The Legal 500 (2010 ed.) for work in this field.  After working with many tax-exempt institutions to navigate the IRS’s implementation of its 2010 global concession, Tom concluded that most of these institutions had arguably been denied the proper amount of interest on their refunds of employer-portion FICA tax.  Again finding himself on the leading edge, Tom represented teaching hospitals seeking to recover $500 to $600 million of additional statutory interest.  Tom is the only lawyer in the nation to have actively pursued additional interest for the teaching hospitals in suits in federal court, filing his first suit in July of 2013.  That huge-dollar, cutting-edge litigation was concluded in October 2019.

Tom has extensive familiarity with new Code section 1061(c)(4)(A), IRS Notice 2018-18, and the new regulation implementing Notice 2018-18 — provisions restricting the tax benefits of Carried Interest, relevant to hedge fund managers.   He is the only tax attorney in the nation to have litigated the scope and meaning of the critical “corporation” term found pervasively across about 600 Code sections and in new section 1061(c)(4)(A).  In that litigation, DOJ/IRS took incoherent positions, inconsistent with the IRS’s announced view in Notice 2018-18.  Opinions issued by the federal courts of appeals in those litigated cases, in which Tom filed over 20 briefs, reflect holdings about the “unambiguous” meaning of “corporation” that are fundamentally inconsistent with Notice 2018-18 and the new regulation.  Tom is the author of the seminal and lauded November 2020 article in Tax Notes on the IRS’s very troubling inconsistency under its regulations and rulings interpreting section 1061(c)(4)(A).

Over the years, Tom has handled cases in court that focused upon the valuation of tangible and intangible property.  He is adept at working with expert witnesses.  He handled one of the first litigated matters to address the valuation of a so-called Core Deposit Intangible, in a depreciation case brought by a South Dakota bank that had acquired acquired another bank.  He was deeply involved in a case brought by a large insurance company to value an insurance-expirations intangible, also sought to be depreciated.  He tried a case to a jury involving the valuation of well-located swamp land donated to a government and deducted as a charitable contribution.

In 1989, Tom was entrusted by the Department of Justice, representing the IRS, with the first-chair in a multi-million dollar gift-tax case in federal court in Minnesota, brought by heirs to the 3M fortune.  The case went to the Court of Appeals for the Eighth Circuit and then to the U.S. Supreme Court, where the IRS was victorious.  United States v. Irvine, 511 U.S. 224 (1994).

Tom represented a billionaire in connection with the IRS’s audit of a large charitable contribution he made to a donor-advised fund.  Tom successfully opposed the IRS’s efforts to take the deposition of the billionaire.  Charitable contributions to a donor-advised fund remain of keen interest to the IRS on audit.

Tom first-chaired a “bet the ESOP” case in U.S. district court in the Southeast in which the IRS and the Department of Justice completely conceded $15 million of excise tax and penalties in connection with a purported prohibited transaction. The case was described in The Legal 500’s law-firm survey for 2009 as reflecting a taxpayer-favorable result that was “most unusual.”

In January 2022, Tom published, in a premier national tax publication, the first article ever on the impact of new FinCEN “beneficial ownership” filing obligations upon the nation’s 30 million small businesses, imposed by 2021’s Corporate Transparency Act and FinCEN’s regulations thereunder.  The first wave of those new obligations will take effect in 2024.  Tom is well positioned to help the officers and beneficial owners of small corporations, LLCs, partnerships, and trusts meet those new reporting obligations.  

Tom’s experience with state and local tax (SALT) matters includes:  a key role in assisting a Racino in recovering $30 million in gaming excise tax; first-chairing a two-day hearing in a charitable property-tax exemption case before an ALJ; formulating arguments, and collecting evidence and preparing witnesses, for a suit by a small business faced with a “bet the company” assessment of lodging excise taxes; and formulating arguments respecting equitable recoupment in a nine-figure California franchise-tax case.

Tom has long been professionally involved with cases raising the question whether Treasury Regulations are authorized and valid, particularly under so-called Chevron Steps Zero, One, and Two.  Tom published the first of his eight articles in this field back in 2001 (Chevron Step Zero) and 2003 (Chevron Step One).  Back in 2011, he guided the briefing of a case that held a Treasury Regulation invalid under Step One. In a case several years ago, his Chevron-related arguments (all steps) prompted the U.S. Department of Justice to eschew, on brief in the Second Circuit, any reliance on a Treasury Regulation that had never been held invalid in any court — a move by DOJ that is believed to be entirely without precedent.  Tom has litigated to a conclusion many cases presenting deference issues, including a  class-action suit seeking roughly $500 to $600 million.  In 2016, he shared an ABA-sponsored panel discussion of Chevron deference with Professor Andy Grewal of the University of Iowa College of Law.  In Nov. 2023, he published yet another article about Chevron, this time in the world’s leading tax publication, Tax Notes Federal and Tax Notes Global. 

In May 2024, he was a panelist on a tax-controversy panel at the 39th Annual Federal Bar Association’s Insurance Tax Seminar; his segment addressed the pending U.S. Supreme Court case, Loper Bright, that would likely make substantial adjustments to the Chevron doctrine.  After the Loper Bright opinion was issued on June 28, 2024, he published, on July 15th, a 5,000-word article about the case and its huge doctrinal  shift in Tax Notes Federal and Tax Notes International, both part of the world’s leading tax publisher.  Tom’s article was chosen, from among many, to be featured on the cover of these 220-page publications.  A copy is available on request.    Loper Bright, having recently overruled Chevron, will now take center stage in cases challenging a Treasury Regulations, including the dubious regulation interpreting new Code section 1061(c)(4)(A) set out in IRS Notice 2018-18 and the ensuing regulations.  In sum, few, if any, tax attorneys in private practice in the U.S. have a deeper, more up-to-date knowledge of, and experience with, the deference to be accorded, or not, to Treasury Regulations.  

An excellent tax lawyer must appreciate existing and emerging nuances in the tax law, and explain them correctly but as simply as possible.   Very often, a correct analysis requires an understanding of how the tax law has changed over the years.  Tax statutes are typically amended in two-year cycles, by each new Congress; and the Treasury Department later follows up with interpretive regulations that ostensibly have the force of law.  Well-informed, keen analysis and clear writing are a tax lawyer’s stock-in-trade.

Tom is the co-author (revisor) of the definitive BNA Tax Management Portfolio (TMP) No. 524, Deductibility of Illegal Payments, Fines and Penalties.  He also is the co-author (revisor) of the chapter of BNA/Bloomberg’s Tax Practice Series (TPS) that addresses IRS audits, assessments, and appeals.   The TMP publication includes a chapter on the Foreign Corrupt Practices Acts (FCPA), which has ever-increasing importance for companies with multinational operations. Further evidence of his intellectual bent is that while he was a law student at Ohio State, he wrote an article on Wisconsin Rule of Evidence 407 that appeared in the Ohio State Law Journal, his law school’s flagship publication.  Tom might be called a “thought leader:” across four different decades, he has published at least 28 articles in tax and non-tax publications.  His writings have been cited by the Supreme Court of Wisconsin; in several leading tax treatises; and in at least 10 law school law reviews, from coast to coast, viz., the American University Law Review, the Creighton University Law Review, the Marquette Law Review, the Nebraska Law Review, the Ohio State Law Journal, the University of Cincinnati Law Review, the University of Miami Law Review, the Missouri Law Review, the New York University School of Law Tax Law Review, and the University of Southern California Law Review.  Tom also has been a frequent media quote source for prominent national publications addressing tax issues of the day.  His original arguments on the invalidity of the IRS’s position on section 1064(c)(4)(A) were repeatedly and favorably addressed by a prominent columnist for Tax Analyst’s Tax Notes publication.  See the drop-down menu for a page listing his many premier publications and media quotes, and his many premier speaking engagements.

Tom formerly was a tax partner, or a tax shareholder, with the Chicago offices of two of the world’s largest and most prestigious international law firms.  After leaving a supervisory position with the U.S. Department of Justice’s Tax Division in 1998, after 14 years, he immediately became a partner with a “K Street” tax boutique in Washington, D.C.  Tom’s nationwide federal tax practice thus brings with it the acumen and connections of a D.C.-based “tax insider,” coupled with a complex-litigation and prosecutorial resume of the highest order.  Over the course of his tax-dispute legal career, Tom has been entrusted with first-chairing $3 to $4 billion of tax disputes in federal court, matching up against many of the nation’s premier tax-dispute lawyers.  Tom has probably first-chaired more $1-million-plus tax refund suits in the federal courts than any other attorney now in private practice in the nation.  This is real-world validation.  

You now have a sense for the breadth and depth of Tom’s top-tier tax-dispute experience — for why he refers to himself as a having a “360-degree resume,” and for how he offers experience-based transitions from IRS Exam or Collection . . . to IRS Appeals, if necessary . . . to a federal trial court, if necessary . . . and to a federal appellate court, if necessary.  No accountant or enrolled agent has trod that path, and only a minuscule percentage of tax lawyers actually has.  A taxpayer facing the IRS ought to know how the path forward looks and will feel, if the hoped-for quick resolution cannot be obtained.        

In recognition of his tax-focused contributions, Tom was again named an Illinois Super Lawyer in Tax for 2021.  Thirteen times Tom has been named an Illinois Super Lawyer in Tax (i.e., Top 5% of all Illinois tax lawyers, as ranked by peers):  2005, 2007, 2010, 2011, 2013-2021.  He is now listed among Washington state Super Lawyers.  He often was named a Leading Illinois Lawyer in Tax Law–Business by the Leading Lawyers Network, including for 2019-2022 (again, Top 5% of all Illinois business tax lawyers as ranked by peers); and named for his work in the tax controversy field in the 2007 and the 2010 and 2011 editions of The Legal 500.  He has been selected as an Illinois Top 100 High-Stakes Litigator in 2020, 2021, 2022, and 2023 (www.Top100HighStakesLitigators.com) (noncompensated selection placing him in the top one-half of one percent of litigators of all types in Illinois and, for 2023, in Washington) — and is one of only six attorneys in the fifty states so recognized who identify tax as a practice area.  While with the U.S. Department of Justice’s Tax Division in DC, Tom received its Outstanding Attorney Award in 1986, 1988, 1991, and 1997, before leaving a GM-15 supervisory post for private practice in DC in 1998.  He thus has received a steady stream of formal, highly coveted accolades from his lawyer peers in the “tax vortices” of DC and Illinois — across five different decades and up through the present.

Tom has a flawless attorney-ethics record, as confirmed by his 10.0/10, “superb” rating at www.avvo.com.

In short, Tom brings a 40-year, award-winning, USDOJ/Mega-Firm tax resume with an intense “360-degree,” billion-dollar complex-litigation perspective, to his own tax-law firm — a firm operating in a highly efficient “boutique” setting . . . a setting without bureaucracy . . . a setting emphatically without any need for an expensive “team” . . . a setting without firm-generated conflicts of interest . . . a setting that eschews fancy artwork and reception areas . . . a setting that uses technology proficiently . . . a setting without money-losing, rate-boosting foreign offices . . . and a setting in Washington state and outside Seattle.  If Tom takes on your dispute, you will get a thoroughly validated, highly efficient tax lawyer with very reasonable fees.  Tom is proud to bring his premier experience and national stature to sparkling Redmond, WA, the epicenter of the world’s digital and AI technology revolutions. 

Your Dispute Is Important, and Concrete Facts Are More Helpful Than Lofty Fluff.  

Practice Areas 

Tom generally limits his nationwide law practice to Federal (i.e., IRS, U.S. Treasury Department, and U.S. Department of Justice) matters:

• Federal trial- and appellate-court tax litigation
• Matters before the IRS.  Holds a PTIN from the IRS, authorizing him to prepare, and supervise the preparation of, amended tax returns, claims for tax refund, and original tax returns — no matter where a taxpayer is located in the U.S.  Holds an EFIN from the IRS, allowing him to e-file certain returns with the IRS for taxpayers — no matter where located.  Holds a CAF from the IRS, allowing him to represent taxpayers, no matter where located, before the IRS under a Power of Attorney, Form 2848.   Holds an authorization to eFile FBARs with FinCEN.  His conduct in federal tax matters before the IRS and Treasury Department is supervised and regulated by the Office of Professional Responsibility (OPR), an office within the Internal Revenue Service in Washington, DC.  He owns a flawless ethics record
• Matters before the U.S. Treasury Department, including Treasury’s FinCEN/BSA operation
• Matters before the U.S. Department of Justice, including the defense of criminal and quasi-criminal investigations
• Matters before other federal agencies, such as the Social Security Administration and the Department of Labor
• All types of matters, tax and non-tax, in Illinois, Wisconsin, and DC — three jurisdictions where he has long and continuously held active, good-standing state bar licenses

Educational Degrees  

• J.D., The Ohio State University, Moritz College of Law, 1979 (graduating at age 24).  Published student note in Ohio State Law Review, 41 Ohio St. L. J. 211 (1980).  The College of Law was ranked 26th (tie) nationally, out of 196 law schools, by the 2024 U.S. News and World Report, a ranking placing it in the sixth position among the Big Ten’s 18 law schools.
• B.A., magna cum laude, University of Wisconsin, Eau Claire, 1976

Bar Admissions (18)

• Actively licensed in Wisconsin (since 1979), the District of Columbia (since 1998), and Illinois (since 2002).  In compliance with CLE requirements for these three state-law jurisdictions.   Not licensed for Washington state-law matters (as opposed to Federal matters)  
• U.S. Supreme Court (in DC; entire U.S.)
• U.S. Court of Appeals for the Second Circuit (NY, CT, VT)
• U.S. Court of Appeals for the Sixth Circuit (OH, MI, KY, TN)
• U.S. Court of Appeals for the Seventh Circuit (IL, WI, IN)
• U.S. Court of Appeals for the Ninth Circuit (AK, AZ, CA, HI, ID, MT, NV, OR, WA)
• U.S. Court of Appeals for the Tenth Circuit (CO, KS, OK, NM, UT, WY)
• U.S. Court of Appeals for the Eleventh Circuit (AL, FL, GA)
• U.S. Court of Appeals for the Federal Circuit (in DC; entire U.S.)
• U.S. District Court, Northern District of Illinois (Chicago)
• Trial Bar, U.S. District Court, Northern District of Illinois (Chicago)
• U.S. District Court, Central District of Illinois
• U.S. District Court, Eastern District of Wisconsin
• U.S. District Court, Western District of Wisconsin
• U.S. District Court, Eastern District of Michigan
• U.S. Tax Court (in DC; entire U.S.)
• U.S. Court of Federal Claims (in DC; entire U.S.)
• Note:  This list does not include various pro hac vice admissions

Professional Memberships

• Member, Tax Advisory Board, The University of Illinois — Chicago Law School (formerly the John Marshall Law School), 2008-2014
• Member, Legal Committee and Safety Committee, Union League Boys & Girls Clubs of Chicago, 2011-2016
• Board of Governors, Court of Federal Claims Bar Association, 2001-2003
• Bar Associations of Wisconsin and DC.

Professional Awards and Recognition

• Profiled, The Ohio State University’s Moritz College of Law’s All Rise Magazine, Winter 2013
• Illinois Super Lawyer for Tax, 2005, 2007, 2010-2011, 2013-2021 — ranked by peers among Top 5% of Tax Lawyers (all types); Illinois Super Lawyer for Appellate, 2017.  Now listed among Washington state Super Lawyers for all of these years.  Noncompensated selection
• Listed, The Legal 500, United States, 2007, 2010-2011.  In 2010, listed for practice in the medical-resident FICA field.  Noncompensated selection
• Listed, Leading Lawyers Network (Illinois), Tax Law — Business (again, Top 5% as selected by Illinois peers), including for 2019-2023.  Noncompensated selection
• Selected as one of Illinois’ Top 100 High Stakes Litigators for 2020-2023 by America’s Top 100 High Stakes Litigators — a non-compensated selection limited to the top one-half of one percent of all Illinois litigators (all types).  (Now listed under Washington state on their website.)
• Rated “Superb” (10.0/10) among tax lawyers by the AVVO algorithmic  lawyer-rating website
• Outstanding Attorney Award, U.S. Department of Justice, Tax Division, Washington, DC, 1986, 1988, 1991, 1997
• Promoted into ascending supervisory, competitive, civil-service positions (GM-15) at the Tax Division, U.S. Department of Justice, Washington, DC, 1991 and 1997; assisted in supervising about 20 U.S. DOJ attorneys.  Promoted, respectively, by the Hon. Shirley D. Peterson and the Hon. Loretta Collins Argrett, Assistant Attorneys General of the Tax Division.  Both were trailblazing luminaries of the national tax bar.  During Tom’s supervisory years, he was directly supervised by the legendary Mildred L. Seidman, Section Chief, who spent more than 50 years at the Tax Division
• His biography appears among Bloomberg Tax’s People on this premier tax publisher’s website
• Unblemished professional ethics record

    Pro Bono

• Appointed by U.S. District Court, N.D. IL, to act as lead counsel for a plaintiff in an employment-discrimination case
• Appointed by the Cook County Circuit Court (IL) to represent an artist involved in a contract dispute
• Judged by invitation at annual ABA National Finals of law student moot court competitions, in Chicago; several years including 2022
• Assisted in a dispute with SSA over tax-driven Medicare benefits
• Countless brief, free consultations with impecunious taxpayers

Maybe Ask: Why Was Tom So Vastly Endorsed and Entrusted, Consistently Over a 40+-Year Period?